After hunting around the iTunes menus, I was unable to find a convenient way to export an entire playlist to a folder that I could drop onto my Android phone.
Then I tried drag and drop…and it worked!
First, connect your phone to your PC. On the phone, pull down the notifications/ongoing bar and tap the USB item. It will probably say “Charge only”. Change this to “Disk drive” and tap “Done”
Then on your computer, open up an Explorer window (Win+E):
Drill into the bigger disk (F: in my case) and look for an MP3 folder. Now go into iTunes and select all the songs you want from the library or a playlist.
Drag those songs into the MP3 folder:
Of course any files with DRM won’t play, but the regular MP3s and unprotected M4As (most of my collection) will work just fine. Let’s see what Android does now. Reverse the above procedure to put the phone back into Charge mode and launch Music:
It takes a little while to build up the lists, but it does work, and you don’t have to wait for it to finish before playing.
Certainly not as slick as an iPod/iPhone, but for occasional (manual) syncing, it does the job.